Synthesis of an epoxide from 1,2-diolDesigning a theoretical synthesis of methamphetamine from phenylpropynePlanes of Symmetry and ChiralityMechanism for synthesis of 4-nitrophenylhydrazine from the diazonium salt of 4-nitroanilineHydrolysis of epoxideBromination of PhenylacetoneHow to rationalise the major product formed in a nucleophile promoted epoxide cleavage reaction?Why is there a need to rotate the molecule in a sharpless asymmetric epoxidation?Reaction of vicinal diol in presence of benzaldehydeTotal number of stereoisomers of 1,2-dimethyl-4-(propan-2-ylidene)cyclopentaneEpoxidation with peroxyacids
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Synthesis of an epoxide from 1,2-diol
Designing a theoretical synthesis of methamphetamine from phenylpropynePlanes of Symmetry and ChiralityMechanism for synthesis of 4-nitrophenylhydrazine from the diazonium salt of 4-nitroanilineHydrolysis of epoxideBromination of PhenylacetoneHow to rationalise the major product formed in a nucleophile promoted epoxide cleavage reaction?Why is there a need to rotate the molecule in a sharpless asymmetric epoxidation?Reaction of vicinal diol in presence of benzaldehydeTotal number of stereoisomers of 1,2-dimethyl-4-(propan-2-ylidene)cyclopentaneEpoxidation with peroxyacids
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$begingroup$
Why is there no formation of epoxide when the two OH-groups are on different planes? I do understand the epoxidation mechanism. However, I would be grateful if someone cleared the specific requirements for epoxidation.
organic-chemistry stereochemistry synthesis
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
$endgroup$
add a comment |
$begingroup$
Why is there no formation of epoxide when the two OH-groups are on different planes? I do understand the epoxidation mechanism. However, I would be grateful if someone cleared the specific requirements for epoxidation.
organic-chemistry stereochemistry synthesis
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
$endgroup$
$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41
add a comment |
$begingroup$
Why is there no formation of epoxide when the two OH-groups are on different planes? I do understand the epoxidation mechanism. However, I would be grateful if someone cleared the specific requirements for epoxidation.
organic-chemistry stereochemistry synthesis
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
$endgroup$
Why is there no formation of epoxide when the two OH-groups are on different planes? I do understand the epoxidation mechanism. However, I would be grateful if someone cleared the specific requirements for epoxidation.
organic-chemistry stereochemistry synthesis
organic-chemistry stereochemistry synthesis
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
edited Jun 30 at 11:16
andselisk♦
21.5k7 gold badges75 silver badges143 bronze badges
21.5k7 gold badges75 silver badges143 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
asked Jun 30 at 10:47
baraah baryhebaraah baryhe
446 bronze badges
446 bronze badges
$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41
add a comment |
$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41
$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41
$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.$Cl^-$ attacks in a $S_N^2$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a $S_N^2$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for $S_N^2$.Therefore
C in your question does not undergo epoxidation.
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
$endgroup$
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
add a comment |
Your Answer
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1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.$Cl^-$ attacks in a $S_N^2$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a $S_N^2$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for $S_N^2$.Therefore
C in your question does not undergo epoxidation.
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
$endgroup$
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
add a comment |
$begingroup$
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.$Cl^-$ attacks in a $S_N^2$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a $S_N^2$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for $S_N^2$.Therefore
C in your question does not undergo epoxidation.
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
$endgroup$
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
add a comment |
$begingroup$
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.$Cl^-$ attacks in a $S_N^2$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a $S_N^2$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for $S_N^2$.Therefore
C in your question does not undergo epoxidation.
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
$endgroup$
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.$Cl^-$ attacks in a $S_N^2$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a $S_N^2$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for $S_N^2$.Therefore
C in your question does not undergo epoxidation.
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
answered Jun 30 at 12:45
Chakravarthy KalyanChakravarthy Kalyan
2,5545 silver badges23 bronze badges
2,5545 silver badges23 bronze badges
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
add a comment |
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
1
1
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
Detailed answer but the OP didn't make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.
$endgroup$
– user55119
Jun 30 at 17:05
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
$begingroup$
@user55119 ,noted,the question was intreasting for an answer.
$endgroup$
– Chakravarthy Kalyan
Jun 30 at 17:14
add a comment |
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$begingroup$
Read up on under what conditions SOCl2 reacts with ROH to give RCl. One set of conditions is SN2; another "internal return", i.e., no inversion.
$endgroup$
– user55119
Jun 30 at 11:41